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Paper | Special issue | Vol 105, No. 1, 2022, pp.487-499
Published online, 26th April, 2022
DOI: 10.3987/COM-22-S(R)20
Synthesis of 1-Azaspiro[4,5]-7-decen-2-one from L-Asparagine and L-Aspartic Acid

Punlop Kuntiyong,* Sunisa Moongmai, Natida Thongluar, and Ittiphat Klayparn

*Department of Chemistry, Faculty of Science, Silpakorn University, Sanamchandra Palace, Muang Nakhon Pathom 73000, Thailand


A synthetic strategy for 1-azaspiro[4.5]-7-decen-2-one based on N-acyliminium spirocyclization is reported. The common core structure found in biologically active alkaloids such as FR901483, TAN1251 and lepadiformine was synthesized via chiral N-alkyl-3-dibenzylaminosuccinimide intermediates. The chiral succinimides were synthesized in 2 steps from L-aspartic acid or 3 steps from L-asparagine.